The nature and relative importance of psychosocial influences on smoking initiation among early adolescents are topics of substantial research interest. Students (n = 1081) from four middle schools were surveyed at the beginning and end of the sixth grade. Baseline predictors were regressed on smoking initiation at end of sixth grade. In bivariate, logistic regression analyses association with problem behaving peers, perceived prevalence, and depression were positively associated and adjustment to school, perceived social competence, parent expectations, parental monitoring, and parental involvement were negatively associated with smoking initiation. In multivariate logistic regression analyses controlling for sex, race, and school, peer affiliation and perceived prevalence were positively associated, whereas social competence and parental monitoring were negatively associated with smoking initiation. A significant interaction between parental involvement and peer affiliation indicated that among teens with problem behaving friends only those with parents who were relatively uninvolved were are at increased risk for smoking initiation. This finding held for boys, girls, Whites, Blacks, and teens living in single parent families. These findings provide evidence that antecedent parenting behaviors may protect early adolescents against smoking even in the context of negative peer affiliation.